Cu(II)‐Catalyzed Enantioselective Aza‐Friedel‐Crafts Reaction of 1‐Naphthols and Electron‐Rich Phenols with Isatin‐Derived Ketimines

Author:

Cai Qihang1,Yu Tianxu1,Li Jiahui1,Zhao Yan1,Hou Jiaqi1,Xue Leipeng1,Yu Shibo1,Yao Chao1,Li Yue‐Ming1ORCID

Affiliation:

1. State Key Laboratory of Medicinal Chemical Biology College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research Nankai University Tianjin 300350 China

Abstract

AbstractNew chiral ligands could be obtained by introducing proline moieties and imidazoline moieties to binaphthyl skeletons. The chiral ligands exhibited balanced rigidity and flexibility which could allow the change of the conformations during the reactions on one hand, and could provide sufficient asymmetric induction on the other. The proline moiety could act as a linker connecting the binaphthyl skeletons and the imidazoline moieties as well as a coordinating group for the central metal, and the electronic and steric properties of the imidazoline groups could be carefully fine‐tuned by the use of different substituents. In the presence of Cu(II) catalyst bearing such chiral ligands, aza‐Friedel–Crafts reaction of 1‐naphthols and electron‐rich phenols with isatin‐derived ketimines provided the desired products with good to excellent yields and up to 99 % ee. The reactions showed good scalability, and excellent ee could still be obtained when the reaction was carried out in gram‐scale.

Funder

National Natural Science Foundation of China

Department of Science and Technology of Shandong Province

Publisher

Wiley

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